2.0 2012-05-31 14:03:25 -0600 2015-09-18 09:17:43 -0600 ECMDB04048 M2MDB000581 3-Dehydro-shikimate 3-dehydro-shikimate is invovled in Chorismic acid biosynthesis. (KEGG) (4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate (4S,5R)-4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylic acid 3-Dehydro-shikimic acid 3-Dehydroshikimate 3-Dehydroshikimic acid 5-Dehydroshikimate 5-Dehydroshikimic acid C7H7O5 171.129 171.029896905 4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate 4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate 10457-99-5 OC1CC(=CC(=O)C1O)C([O-])=O InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/p-1 SLWWJZMPHJJOPH-UHFFFAOYSA-M Solid Cytosol logp -1.23 ALOGPS logs 0.27 ALOGPS solubility 3.56e+02 g/l ALOGPS logp -1 ChemAxon pka_strongest_acidic 3.21 ChemAxon pka_strongest_basic -3.3 ChemAxon iupac 4,5-dihydroxy-3-oxocyclohex-1-ene-1-carboxylate ChemAxon average_mass 171.129 ChemAxon mono_mass 171.029896905 ChemAxon smiles OC1CC(=CC(=O)C1O)C([O-])=O ChemAxon formula C7H7O5 ChemAxon inchi InChI=1S/C7H8O5/c8-4-1-3(7(11)12)2-5(9)6(4)10/h1,5-6,9-10H,2H2,(H,11,12)/p-1 ChemAxon inchikey SLWWJZMPHJJOPH-UHFFFAOYSA-M ChemAxon polar_surface_area 97.66 ChemAxon refractivity 49.03 ChemAxon polarizability 14.58 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 5 ChemAxon donor_count 2 ChemAxon physiological_charge -1 ChemAxon formal_charge -1 ChemAxon Phenylalanine, tyrosine and tryptophan biosynthesis ec00400 Metabolic pathways eco01100 Chorismate biosynthesis Chorismate is an intermediate in the synthesis of three amino acids: tyrosine, phenylalanine and tryptophan. In addition it is a precursor of folic acid, ubiquinone, menaquinone, and enterochelin. The first reaction in the chorismate pathway is catalyzed by three separate enzymes, all involved in the biosynthesis of Shikimic acid, each of which is subject to feedback inhibition by one of the three amino acids. However, even in the presence of all three amino acids, sufficient enzymatic activity is present to permit synthesis of the other four metabolites synthesized from chorismate because the enzyme subject to regulation by tryptophan cannot be inhibited more than 60 percent. The biosynthesis of chorismate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving Quinate/shikimate dehydrogenase and shikimate dehydrogenase 2. Shikimic acid is phosphorylated by Shikimate kinase 2 into shikimate 3-phosphate. Shikimate 3- phophate and a phosphoenolpyruvic acid are then joined through a 3-phosphoshikimate 1-carboxyvinyltransferase to produce a 5-enoylpyruvyl-shikimate 3-phosphate while releasing a phosphate. This in turns produces our final product Chorismate through a chorismate synthase. PW000816 Metabolic Secondary Metabolites: Shikimate Pathway The biosynthesis of shikimate starts with D-Erythrose-4-phosphate getting transformed into 3-deoxy-D-arabino-heptulosonate-7-phosphate through a phospho-2-dehydro-3-deoxyheptonate aldolase. This is followed by a 3-dehydroquinate synthase converting the 3-deoxy-D-arabino-heptulosonate-7-phosphate into a 3-dehydroquinate which in turn is conveted to 3-dehydroshikimate through a 3-dehydroquinate dehydratase. A this point 3-dehydroshikimate can be turned into Shikimic acid through 2 different reactions involving an NADPH driven Quinate/shikimate dehydrogenase or a NADPH driven shikimate dehydrogenase 2. Shikimate can also be transported through a shikimate:H+ symporter. PW000985 Metabolic chorismate biosynthesis from 3-dehydroquinate PWY-6163 Specdb::NmrOneD 275978 Specdb::NmrOneD 275979 Specdb::NmrOneD 275980 Specdb::NmrOneD 275981 Specdb::NmrOneD 275982 Specdb::NmrOneD 275983 Specdb::NmrOneD 275984 Specdb::NmrOneD 275985 Specdb::NmrOneD 275986 Specdb::NmrOneD 275987 Specdb::NmrOneD 275988 Specdb::NmrOneD 275989 Specdb::NmrOneD 275990 Specdb::NmrOneD 275991 Specdb::NmrOneD 275992 Specdb::NmrOneD 275993 Specdb::NmrOneD 275994 Specdb::NmrOneD 275995 Specdb::NmrOneD 275996 Specdb::NmrOneD 275997 Specdb::MsMs 1401214 Specdb::MsMs 1401215 Specdb::MsMs 1401216 5460360 4573915 C02637 16630 3-DEHYDRO-SHIKIMATE Keseler, I. M., Collado-Vides, J., Santos-Zavaleta, A., Peralta-Gil, M., Gama-Castro, S., Muniz-Rascado, L., Bonavides-Martinez, C., Paley, S., Krummenacker, M., Altman, T., Kaipa, P., Spaulding, A., Pacheco, J., Latendresse, M., Fulcher, C., Sarker, M., Shearer, A. G., Mackie, A., Paulsen, I., Gunsalus, R. P., Karp, P. D. (2011). "EcoCyc: a comprehensive database of Escherichia coli biology." Nucleic Acids Res 39:D583-D590. 21097882 Kanehisa, M., Goto, S., Sato, Y., Furumichi, M., Tanabe, M. (2012). "KEGG for integration and interpretation of large-scale molecular data sets." Nucleic Acids Res 40:D109-D114. 22080510 van der Werf, M. J., Overkamp, K. M., Muilwijk, B., Coulier, L., Hankemeier, T. (2007). "Microbial metabolomics: toward a platform with full metabolome coverage." Anal Biochem 370:17-25. 17765195 Winder, C. L., Dunn, W. B., Schuler, S., Broadhurst, D., Jarvis, R., Stephens, G. M., Goodacre, R. (2008). "Global metabolic profiling of Escherichia coli cultures: an evaluation of methods for quenching and extraction of intracellular metabolites." Anal Chem 80:2939-2948. 18331064 3-dehydroquinate dehydratase P05194 AROD_ECOLI aroD http://ecmdb.ca/proteins/P05194.xml Quinate/shikimate dehydrogenase P0A6D5 YDIB_ECOLI ydiB http://ecmdb.ca/proteins/P0A6D5.xml Shikimate dehydrogenase P15770 AROE_ECOLI aroE http://ecmdb.ca/proteins/P15770.xml 3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid R02413 SHIKIMATE-5-DEHYDROGENASE-RXN 3-Dehydroquinate <> 3-Dehydro-shikimate + Water R03084 3-DEHYDROQUINATE-DEHYDRATASE-RXN Shikimic acid + NADP <> 3-Dehydro-shikimate + NADPH + Hydrogen ion R02413 Shikimic acid + NAD <> 3-Dehydro-shikimate + NADH + Hydrogen ion R06847 NAD(P)⁺ + Shikimic acid < NAD(P)H + 3-Dehydro-shikimate + Hydrogen ion RXN-7968 NADP + Shikimic acid < Hydrogen ion + NADPH + 3-Dehydro-shikimate SHIKIMATE-5-DEHYDROGENASE-RXN Quinate + NAD + NADP + Shikimic acid <> 3-Dehydroquinate + NADH + NADPH + Hydrogen ion + 3-Dehydro-shikimate R01872 R06846 3-Dehydroquinate > Water + 3-dehydroshikimate + 3-Dehydro-shikimate PW_R002912 3-dehydroshikimate + Hydrogen ion + NADPH + 3-Dehydro-shikimate + NADPH > NADP + Shikimic acid PW_R002913 3 3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid 3 3-Dehydro-shikimate + Hydrogen ion + NADPH <> NADP + Shikimic acid